EP0965621A1 - Masses durcissables par irradiations contenant des dérivés d'acide phénylglyoxylique - Google Patents

Masses durcissables par irradiations contenant des dérivés d'acide phénylglyoxylique Download PDF

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Publication number
EP0965621A1
EP0965621A1 EP99111279A EP99111279A EP0965621A1 EP 0965621 A1 EP0965621 A1 EP 0965621A1 EP 99111279 A EP99111279 A EP 99111279A EP 99111279 A EP99111279 A EP 99111279A EP 0965621 A1 EP0965621 A1 EP 0965621A1
Authority
EP
European Patent Office
Prior art keywords
radiation
curable
weight
compositions according
curable compositions
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP99111279A
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German (de)
English (en)
Inventor
Reinhold Dr. Schwalm
Erich Dr. Beck
Rainer Dr. Königer
Uwe Dr. Meisenburg
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF SE
Original Assignee
BASF SE
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by BASF SE filed Critical BASF SE
Publication of EP0965621A1 publication Critical patent/EP0965621A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/81—Unsaturated isocyanates or isothiocyanates
    • C08G18/8141—Unsaturated isocyanates or isothiocyanates masked
    • C08G18/815—Polyisocyanates or polyisothiocyanates masked with unsaturated compounds having active hydrogen
    • C08G18/8158—Polyisocyanates or polyisothiocyanates masked with unsaturated compounds having active hydrogen with unsaturated compounds having only one group containing active hydrogen
    • C08G18/8175—Polyisocyanates or polyisothiocyanates masked with unsaturated compounds having active hydrogen with unsaturated compounds having only one group containing active hydrogen with esters of acrylic or alkylacrylic acid having only one group containing active hydrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/08—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated side groups
    • C08F290/14—Polymers provided for in subclass C08G
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/67—Unsaturated compounds having active hydrogen
    • C08G18/671—Unsaturated compounds having only one group containing active hydrogen
    • C08G18/672—Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
    • C09D4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09D159/00 - C09D187/00

Definitions

  • the invention relates to the use of radiation-curable composition as a coating agent, in particular outdoors, e.g. for painting motor vehicles or Automotive parts.
  • Radiation-curable compositions have so far mainly been used for Coating wood, paper and plastics indoors used. For outdoor applications there is a resistance to Weather influences, a low tendency to yellowing and high Hydrolysis stability required.
  • UV absorbers and Radical scavengers necessary.
  • the principal problem here is that these masses for outdoor use on the one hand despite the content of UV absorbers photochemically induced radical hardening and on the other hand after hardening despite the content required for the hardening Photoinitiators are stable against UV light.
  • radiation-curable compositions generally always have a strong Initial yellowing on.
  • Phenylglyoxylic acid and its derivatives are as photoinitiators known. In "Applied Macromolecular Chemistry 1981, 93 (1), page 83-95 are described by Wolfram Mayer et al. Ammonium salts of Phenylglyoxylic acid and its use i.a. in paints Isocyanate base described. Cause ammonium-containing compounds slightly yellowing, such photoinitiators come therefore not considered for outdoor applications. Task of the present Invention were therefore weather-stable radiation-curable Masses.
  • the radiation-curable materials defined at the outset were accordingly Masses and their use as a coating mass outdoors found.
  • the radiation-curable compositions according to the invention necessarily contain a photoinitiator P1, which is phenylglyoxylic acid, its esters or salts, with the exception of the ammonium salts, or derivatives of these compounds.
  • a photoinitiator P1 which is phenylglyoxylic acid, its esters or salts, with the exception of the ammonium salts, or derivatives of these compounds.
  • the derivatives are in particular compounds with substituents on the phenyl ring, for example the radicals R 2 and R 3 below.
  • Suitable salts of phenylglyoxylic acid are e.g. the Salts of alkali metals, especially lithium, sodium and Potassium.
  • R 2 and R 3 are preferably independently of one another an H atom.
  • the phenyl ring is preferably substituted in the para position (4 position) to the carbonyl group.
  • the essential feature of the photoinitiators P1 is the structural element the phenyl ring can of course be further substituted.
  • Compounds are also suitable which contain the above structural element more often, for example 2-4 times.
  • Such compounds are obtainable, for example, by esterifying phenylglyoxylic acid with polyhydric alcohols, e.g. B. with C 2 -C 8 diols, triplets or tetraols, ethylene glycol, propylene glycol, trimethylolpropane, glycerol etc. may be mentioned
  • the structural feature becomes independent of others Substituents on the phenyl ring calculated at 133 g / mol and on the Total weight of the respective photoinitiator P1 related.
  • the photoinitiator P1 can be used alone or as a mixture with others Photoinitiators can be used. So far mixtures for use come, they preferably contain at least 20% by weight, particularly preferably at least 35% by weight, very particularly preferably at least 50% by weight of a photoinitiator P1, based on the total amount of photoinitiators.
  • Photoinitiators which are used in a mixture with P1, e.g. Mono- or bisacylphosphine oxides, benzophenones or Hydroxyacetophenones.
  • Radiation-curable compounds are ethylenically unsaturated, Radically copolymerizable compounds.
  • urethane acrylates should also include the corresponding methacrylates.
  • Urethane acrylates can be obtained by reacting polyisocyanates with hydroxyalkyl (meth) acrylates and optionally Chain extenders such as diols, polyols, diamines, polyamines or dithiols or polythiols.
  • Chain extenders such as diols, polyols, diamines, polyamines or dithiols or polythiols.
  • Emulsifiers also contain dispersible urethane acrylates still ionic and / or non-ionic hydrophilic groups, which e.g. through structural components such as hydroxycarboxylic acids Urethane acrylate are introduced.
  • the urethane acrylates preferably have a number average Molecular weight from 1000 to 30 000, especially from 1500 to 20,000 g / mol (determined by gel permeation chromatography with Polystyrene as standard).
  • the urethane acrylates preferably have a content of 1 to 5, particularly preferably from 2 to 4 and very particularly preferably from 2 to 3 moles of (meth) acrylic groups per 1000 g of urethane acrylate.
  • Aliphatic polyisocyanates are preferred, the term aliphatic also non-aromatic alicyclic compounds should include.
  • Preferred urethane acrylates are aliphatic urethane acrylates a), which aromatic ring systems at most in subordinate ones Amounts of e.g. less than 5% by weight, based on the urethane acrylates, and particularly preferably no aromatic ring systems contain.
  • the radiation-curable composition can do other things ethylenically unsaturated, radically polymerizable Connections included.
  • Poly (meth) acrylates b) of aliphatic ones are particularly suitable Polyols, especially 2 to 5 alcohols, the in addition to the hydroxyl groups, no other functional groups or possibly contain ether groups.
  • Examples of such alcohols are bifunctional alcohols, such as Ethylene glycol, propylene glycol, and their more condensed ones Representatives, e.g. such as diethylene glycol, triethylene glycol, Dipropylene glycol, tripropylene glycol ect., Butanediol, pentanediol, Hexanediol, neopentylglycol, cyclohexanedimethanol, trifunctional and higher functional alcohols, such as glycerin, trimethylolpropane, Butanetriol, trimethylolethane, pentaerythritol, ditrimethylolpropane, Dipentaerythritol, sorbitol, mannitol and the corresponding alkoxylated, especially ethoxy and propoxylated alcohols.
  • bifunctional alcohols such as Ethylene glycol, propylene glycol, and their more condensed ones Representatives, e.g
  • Suitable poly (meth) acrylates b) in particular have a molecular weight below 1000 g / mol, particularly preferably below 600 g / mol and have 2 to 4 (meth) acrylic groups in the molecule, i.e. it is a matter of Di-, tri or tetraacrylates.
  • Polyester acrylates epoxy acrylates or also monoacrylates such as butyl acrylate, cyclohexyl acrylate ect. Monoacrylates are used especially as additional Reactive thinner used.
  • the radiation-curable compositions can also be radiation-curable Contain compounds without acrylic groups (connections d)).
  • Containing vinyl or allyl groups Compounds such as vinyl esters, aromatic vinyl compounds, e.g. Styrene, vinyl ethers, their oligomers or polymers, including unsaturated ones Polyester ect.
  • the radiation-curable compounds Preferably containing the radiation-curable compounds only little or no aromatic components.
  • the content of aromatic carbon atoms i.e. carbon atoms, the components of a aromatic ring system
  • the radiation-curable compounds can be in the radiation-curable Bulk solvent-free, dissolved in organic Solvents or dispersed in water.
  • Solvent-free and especially aqueous are preferred Systems.
  • the radiation-curable compounds can with the help of Emulsifiers or protective colloids are dispersed in water, if the compounds are not already in a content of hydrophilic groups themselves are dispersible.
  • the radiation-curable compositions can contain further components contain.
  • Pigments and leveling agents should be mentioned in particular and stabilizers.
  • UV absorbers convert UV radiation into thermal energy.
  • Known UV absorbers are hydroxybenzophenones, benzotriazoles, cinnamic acid esters and oxalanilides.
  • Radical scavengers bind radicals that are formed as intermediates.
  • Significant Radical scavengers are sterically hindered amines, which are called HALS (Hindered Amine Light Sabilizers) are known.
  • the content of UV absorbers and is for outdoor applications Radical scavengers in total preferably 0.1 to 5 parts by weight, particularly preferably 0.5 to 4 parts by weight, based on 100 parts by weight of radiation-curable compounds.
  • the radiation-curable composition can be radiation-curable Connections also contain connections that contribute to hardening through other chemical reactions.
  • connections that contribute to hardening through other chemical reactions.
  • Polyisocyanates which with hydroxyl or Network amine groups.
  • the radiation-curable compositions are suitable as coating compositions.
  • substrates e.g. Metal, wood, Plastic into consideration. It can be protective coatings or act decorative coatings.
  • Such applications are e.g. Exterior coatings of buildings or parts of buildings, coatings on vehicles, in particular on motor vehicles such as passenger cars, trucks (short Automobiles), rail vehicles, airplanes.
  • the radiation-curable compositions according to the invention are suitable especially as a clear coat (also top coat) of motor vehicles.
  • the clear coat of a motor vehicle is the outermost one Lacquer layer exposed to weather.
  • the radiation-curable coating compositions can by the known methods on the substrates to be coated be applied.
  • order processes come into consideration like spraying, rolling up, doctoring.
  • the curing can be done by radiation curing with UV light, which may include the UV component of daylight can suffice.
  • UV light which may include the UV component of daylight can suffice.
  • commercial UV lamps are preferred used for radiation curing.
  • Masses show a high resistance against Weather influences, especially a low tendency to yellowing and high hydrolysis stability. In particular, theirs too the initial yellowing that often occurs during UV curing observe.
  • a lacquer is produced from 70% by weight of a reaction product of hydroxyethyl acrylate with the isocyanurate of Hexamethylene diisocyanate, 30% by weight hexanediol diacrylate and 4 % By weight, based on the total amount of the acrylates, of the photoinitiator Phenylglyoxylic acid methyl ester.
  • the lacquer is applied to a white lacquered sheet with a box doctor blade with a 200 ⁇ m gap and cured at 10 m / min in an IST exposure system with approximately 1800 mJ / cm 2 .
  • the b * which is a measured value for the yellowing, is determined in accordance with DIN 6174.
  • the temperature was 37 ° C.
  • the b * value is 2.5.
  • the sheets are subjected to the Suntest (Heaeus Suntest CPS +) accelerated conditions in their tendency to yellowing on day or Sunlight examined.
  • the temperature in the test room was 37 ° C.
  • a lacquer is produced from 70% by weight of one Reaction product of hydroxyethyl acrylate with the isocyanurate of hexamethylene diisocyanate, 30% by weight of hexanediol diacrylate and 4 wt .-%, based on the total amount of acrylates, the Photoinitiators phenylglyoxylic acid.
  • the lacquer is applied to a white lacquered sheet with a box doctor blade with a 200 ⁇ m gap and cured at 10 m / min in an IST exposure system with approximately 1800 mJ / cm 2 .
  • the b * value is determined colorimetrically.
  • Time after loading (H) Example 2 0 1.9 0.5 1.4 1 1.2 5 0.8 24th 0.7

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Paints Or Removers (AREA)
  • Macromonomer-Based Addition Polymer (AREA)
  • Application Of Or Painting With Fluid Materials (AREA)
  • Polymerisation Methods In General (AREA)
EP99111279A 1998-06-16 1999-06-10 Masses durcissables par irradiations contenant des dérivés d'acide phénylglyoxylique Withdrawn EP0965621A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19826712 1998-06-16
DE1998126712 DE19826712A1 (de) 1998-06-16 1998-06-16 Strahlungshärtbare Massen, enthaltend Phenylglyoxylate

Publications (1)

Publication Number Publication Date
EP0965621A1 true EP0965621A1 (fr) 1999-12-22

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EP99111279A Withdrawn EP0965621A1 (fr) 1998-06-16 1999-06-10 Masses durcissables par irradiations contenant des dérivés d'acide phénylglyoxylique

Country Status (3)

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EP (1) EP0965621A1 (fr)
JP (1) JP2000126682A (fr)
DE (1) DE19826712A1 (fr)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6562464B1 (en) 1999-03-24 2003-05-13 Basf Aktiengesellschaft Utilization of phenylglyoxalic acid esters as photoinitiators
GB2401561A (en) * 2003-04-11 2004-11-17 Pal Group Plc A profile element provided with a decorative layer and a UV stable layer
US6987135B2 (en) 2000-10-25 2006-01-17 Akzo Nobel N.V. Photoactivatable water borne coating composition
US7605209B2 (en) 2003-06-12 2009-10-20 Valspar Sourcing, Inc. Coating compositions containing reactive diluents and methods
US7728068B2 (en) 2003-06-12 2010-06-01 Valspar Sourcing, Inc. Coating compositions containing reactive diluents and methods
US7863583B2 (en) 2004-06-24 2011-01-04 Basf Aktiengesellschaft Device and process for curing using energy-rich radiation in an inert gas atmosphere
AU2005309870B2 (en) * 2004-11-22 2011-03-03 Valspar Sourcing, Inc. Coating composition and methods
WO2024150128A1 (fr) * 2023-01-11 2024-07-18 Consorcio Comex, S.A. De C.V. Composition de revêtement hybride acrylique et polyuréthane

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10241299A1 (de) 2002-09-04 2004-03-25 Basf Ag Strahlungshärtbare Polyurethane mit verkappten Aminogrupppen
DE10348463A1 (de) 2003-10-14 2005-05-25 Basf Ag Hyperverzweigte Polyester mit ethylenisch ungesättigten Gruppen
KR100735810B1 (ko) 2004-06-03 2007-07-06 주식회사 엘지화학 광디스크용 자외선 경화 수지 조성물
DE102004063102A1 (de) 2004-12-22 2006-07-13 Basf Ag Strahlungshärtbare Verbindungen
JP5421533B2 (ja) * 2004-12-22 2014-02-19 チバ ホールディング インコーポレーテッド 強接着性コーティングの製造方法
KR101251244B1 (ko) 2005-02-24 2013-04-08 바스프 에스이 방사선 경화성 수성 폴리우레탄 분산액
DE102005010109A1 (de) 2005-03-02 2006-09-07 Basf Ag Modifizierte Polyolefinwachse
DE102005057683A1 (de) 2005-12-01 2007-06-06 Basf Ag Strahlungshärtbare wasserelmulgierbare Polyisocyanate
CN101616946B (zh) 2007-02-15 2012-07-18 巴斯夫欧洲公司 聚氨酯分散体及其制备和用途
DE102007026196A1 (de) 2007-06-04 2008-12-11 Basf Se Verfahren zur Herstellung wasseremulgierbarer Polyurethanacrylate
DE102008002008A1 (de) 2007-06-04 2008-12-11 Basf Se Verfahren zur Herstellung wasseremulgierbarer Polyurethanacrylate
US8193279B2 (en) 2007-06-21 2012-06-05 Basf Se Flexible, radiation-curable coating compositions
EP2160423A1 (fr) 2007-06-21 2010-03-10 Basf Se Matériaux de revêtement durcissables par rayonnement présentant une adhérence élevée
DE102008041654A1 (de) 2007-08-31 2009-03-05 Basf Se Neue Beschichtungsmittel
DE102008043202A1 (de) 2007-10-29 2009-04-30 Basf Se Verfahren zur Kantenleimung von Textilien
DE102009046713A1 (de) 2008-11-27 2010-06-02 Basf Se Strahlungshärtbare Beschichtungsmassen
DE102010001956A1 (de) 2009-02-17 2010-08-19 Basf Se Verfahren zur Herstellung wasseremulgierbarer Polyurethanacrylate
US9200108B2 (en) 2009-03-24 2015-12-01 Basf Se Radiation-curing, highly functional polyurethane (meth)acrylate
DE102010003308A1 (de) 2009-03-31 2011-01-13 Basf Se Strahlungshärtbare wasseremulgierbare Polyurethan(meth)acrylate
WO2010121978A1 (fr) 2009-04-22 2010-10-28 Basf Se Matières de revêtement durcissables par rayonnement
US8415437B2 (en) 2009-08-05 2013-04-09 Basf Se (Meth)acrylated melamine formaldehyde resins
WO2011015540A1 (fr) 2009-08-06 2011-02-10 Basf Se Polyuréthannes hydrodispersibles, durcissant aux rayonnements et dispersions de polyuréthanne correspondantes
DE102010044204A1 (de) 2009-11-25 2011-05-26 Basf Se Verfahren zur Herstellung von strahlungshärtbaren (Meth)Acrylaten
DE102010044206A1 (de) 2009-11-25 2011-05-26 Basf Se Verfahren zur Herstellung von strahlungshärtbaren (Meth)Acrylaten
DE102010026490A1 (de) 2010-07-07 2012-01-12 Basf Se Verfahren zur Herstellung von feinstrukturierten Oberflächen
US9090736B2 (en) 2011-02-22 2015-07-28 Basf Se Rheological agent for radiation-curable coating compositions
PL2678364T3 (pl) 2011-02-22 2015-08-31 Basf Se Środek reologiczny do radiacyjnie utwardzalnych mas powłokowych
CN103608375B (zh) 2011-06-14 2015-09-09 巴斯夫欧洲公司 可辐射固化聚氨酯水分散体
WO2013110504A1 (fr) 2012-01-27 2013-08-01 Basf Se Revêtements antimicrobiens durcissables sous l'action d'un rayonnement
US8728455B2 (en) 2012-01-27 2014-05-20 Basf Se Radiation-curable antimicrobial coatings
WO2013110566A1 (fr) 2012-01-27 2013-08-01 Basf Se Matière de revêtement antimicrobienne durcissable par rayonnement
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EP2828348B1 (fr) 2012-03-19 2016-04-20 Basf Se Compositions de revêtements durcissables par rayonnement
US9193888B2 (en) 2012-03-19 2015-11-24 Basf Se Radiation-curable aqueous dispersions
WO2013178523A1 (fr) 2012-05-30 2013-12-05 Basf Se Composes durcissables par rayonnement
US9296907B2 (en) 2012-05-30 2016-03-29 Basf Se Radiation-curable compounds
CN104470997B (zh) 2012-07-20 2016-08-17 巴斯夫欧洲公司 快速干燥的可辐照固化的涂料混合物
EP2882808B1 (fr) 2012-08-09 2016-10-12 Basf Se Formulations à forte adhérence durcissables par rayonnement
KR101382432B1 (ko) * 2012-08-30 2014-04-08 유니온스틸 주식회사 고선영성 칼라강판 및 그 제조방법
CA2885130A1 (fr) 2012-10-24 2014-05-01 Basf Se (meth)acrylates de polyurethane radiodurcissables dispersibles dans l'eau
PL2920222T3 (pl) 2012-11-16 2017-09-29 Basf Se Poliuretany, ich dyspersje, ich wytwarzanie i zastosowanie
EP2931811A2 (fr) 2012-12-14 2015-10-21 Basf Se Résines aminiques (méth)acrylées
WO2014161817A1 (fr) 2013-04-03 2014-10-09 Basf Se Procédé de réduction de la quantité de monomère résiduelle dans une dispersion polymère aqueuse
WO2015028397A1 (fr) 2013-08-26 2015-03-05 Basf Se (méth)acrylates de polyuréthane dispersibles dans l'eau et durcissables sous l'effet d'un rayonnement
PL3058008T3 (pl) 2013-10-16 2017-12-29 Basf Se Zastosowanie emulgowalnych w wodzie poliuretanoakrylanów
ES2642377T3 (es) 2013-11-05 2017-11-16 Construction Research & Technology Gmbh Recubrimientos para uso como adhesivos
ES2656120T5 (en) 2014-01-14 2026-04-08 Lignum Tech Ag Layered building board for inside and outside
EP2942361A1 (fr) 2014-05-06 2015-11-11 Basf Se Amélioration de grain avec des agents tensioactifs dans des dispersions de polyuréthane durcissable aux uv à base d'eau
PL3201261T3 (pl) 2014-10-01 2019-07-31 Basf Se Sposób utwardzania utwardzalnych kompozycji
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US20160223269A1 (en) 2015-02-04 2016-08-04 Outlast Technologies, LLC Thermal management films containing phase change materials
US10003053B2 (en) 2015-02-04 2018-06-19 Global Web Horizons, Llc Systems, structures and materials for electrochemical device thermal management
US10431858B2 (en) 2015-02-04 2019-10-01 Global Web Horizons, Llc Systems, structures and materials for electrochemical device thermal management
KR20180041165A (ko) 2015-08-17 2018-04-23 바스프 에스이 폴리우레탄 (메트)아크릴레이트를 포함하는 수성 중합체 조성물
EP3173449A1 (fr) 2015-11-27 2017-05-31 BASF Coatings GmbH Composite a partir de deux corps solides
CA3033081C (fr) 2016-08-19 2023-12-05 Xylo Technologies Ag Panneau revetu et son procede de fabrication
JP1609254S (fr) 2017-04-03 2018-07-17
DK3820927T3 (da) 2018-07-13 2024-10-07 Miwon Austria Forschung Und Entw Gmbh Vanddispergible polyurethan (meth)akrylater til aktiniske strålingshærdende belægninger
WO2021069295A1 (fr) 2019-10-08 2021-04-15 Basf Se Composés de revêtement à deux composants durcissables thermiquement
DE102020132126A1 (de) 2020-12-03 2022-06-09 Leibniz-Institut Für Neue Materialien Gemeinnützige Gesellschaft Mit Beschränkter Haftung Strukturiertes Material
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EP4504494A1 (fr) 2022-04-06 2025-02-12 Basf Se Composition durcissable pour procédé d'impression 3d et objet imprimé en 3d formé à partir de celle-ci et procédé d'impression 3d l'utilisant
WO2024141320A1 (fr) 2022-12-29 2024-07-04 Basf Se Composition liquide durcissable par rayonnement, procédé de formation d'un objet imprimé en 3d et objet imprimé en 3d
WO2024160696A2 (fr) 2023-01-31 2024-08-08 Basf Se Composition durcissable, objet imprimé en 3d constitué à partir de celle-ci et son procédé de formage

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3930868A (en) * 1973-05-23 1976-01-06 The Richardson Company Light sensitive arylglyoxyacrylate compositions
US4234739A (en) * 1978-12-05 1980-11-18 Stauffer Chemical Company Method for preparing glyoxylic acids and derivatives thereof
US4279720A (en) * 1978-07-13 1981-07-21 Ciba-Geigy Corporation Photocurable composition
US5387304A (en) * 1988-09-27 1995-02-07 Ciba-Geigy Corporation Application of a painted carrier film to a three-dimensional substrate

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3930868A (en) * 1973-05-23 1976-01-06 The Richardson Company Light sensitive arylglyoxyacrylate compositions
US4279720A (en) * 1978-07-13 1981-07-21 Ciba-Geigy Corporation Photocurable composition
US4234739A (en) * 1978-12-05 1980-11-18 Stauffer Chemical Company Method for preparing glyoxylic acids and derivatives thereof
US5387304A (en) * 1988-09-27 1995-02-07 Ciba-Geigy Corporation Application of a painted carrier film to a three-dimensional substrate

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6562464B1 (en) 1999-03-24 2003-05-13 Basf Aktiengesellschaft Utilization of phenylglyoxalic acid esters as photoinitiators
US6987135B2 (en) 2000-10-25 2006-01-17 Akzo Nobel N.V. Photoactivatable water borne coating composition
GB2401561A (en) * 2003-04-11 2004-11-17 Pal Group Plc A profile element provided with a decorative layer and a UV stable layer
GB2401561B (en) * 2003-04-11 2006-06-07 Pal Group Plc Profile element
US7605209B2 (en) 2003-06-12 2009-10-20 Valspar Sourcing, Inc. Coating compositions containing reactive diluents and methods
US7728068B2 (en) 2003-06-12 2010-06-01 Valspar Sourcing, Inc. Coating compositions containing reactive diluents and methods
AU2004248127B2 (en) * 2003-06-12 2011-01-27 Valspar Sourcing Inc. Coating compositions containing reactive diluents and methods
US9469780B2 (en) 2003-06-12 2016-10-18 Valspar Sourcing, Inc. Coating compositions containing reactive diluents and methods
US7863583B2 (en) 2004-06-24 2011-01-04 Basf Aktiengesellschaft Device and process for curing using energy-rich radiation in an inert gas atmosphere
AU2005309870B2 (en) * 2004-11-22 2011-03-03 Valspar Sourcing, Inc. Coating composition and methods
US7923513B2 (en) 2004-11-22 2011-04-12 Valspar Sourcing, Inc. Coating compositions and methods
WO2024150128A1 (fr) * 2023-01-11 2024-07-18 Consorcio Comex, S.A. De C.V. Composition de revêtement hybride acrylique et polyuréthane

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